Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
  • C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
  • C09B62/507—Azo dyes
  • C09B62/513—Disazo or polyazo dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0046—Mixtures of two or more azo dyes
  • C09B67/0047—Mixtures of two or more reactive azo dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0046—Mixtures of two or more azo dyes
  • C09B67/0055—Mixtures of two or more disazo dyes
  • C09B67/0057—Mixtures of two or more reactive disazo dyes
  • C09B67/0059—Mixtures of two or more reactive disazo dyes all the reactive groups are not directly attached to a heterocyclic system
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/30—Inkjet printing inks
  • C09D11/32—Inkjet printing inks characterised by colouring agents
  • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
  • D06P1/384—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group not directly attached to heterocyclic group
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
  • D06P5/30—Ink jet printing

Definitions

• Fiber-reactive azo dyes and dye mixtures, preparation thereof and use thereof are Fiber-reactive azo dyes and dye mixtures, preparation thereof and use thereof
• the invention is situated within the technical field of fiber-reactive azo dyes.
• the invention now present has succeeded in providing dyes which to a high demand meet the requirements for buildup, wash-off ability, and fastnesses.
• the present invention provides azo dyes of the formula (1 )
• Z is an alkali-detachable group
• R is a radical -COOR 1 , -CN or -CONR 2 R 3 , in which
• R 1 is M or (Ci-C 4 )-alkyl
• R 2 and R 3 independently of one another are hydrogen or (Ci-C 4 )-alkyl; and M is hydrogen, ammonium, an alkali metal, or the equivalent of an alkaline earth metal.
• Alkali-detachable groups Z are, for example, halogen atoms, such as chlorine and bromine, ester groups of organic carboxylic and sulfonic acids, examples being alkylcarboxylic acids, unsubstituted or substituted benzenecarboxylic acids, and unsubstituted or substituted benzenesulfonic acids, more particularly alkanoyloxy of 2 to 5 carbon atoms such as acetyloxy, and also benzoyloxy, sulfobenzoyloxy, phenylsulfonyloxy and tolylsulfonyloxy, and also acidic ester groups of inorganic acids, such as of phosphoric acid, sulfuric acid, and thiosulfuhc acid (phosphato, sulfato and thiosulfato groups), and also dialkylamino groups with alkyl groups each of 1 to 4 carbon atoms, such as dimethylamino and diethylamino
• the group -SO 2 Z may be present partly as vinylsulfonyl and partly as -SO 2 CH 2 CH 2 Z, preferably as ⁇ -sulfatoethylsulfonyl.
• the fraction of the respective dye with the vinylsulfonyl group in this case is more particularly up to about 30 mol%, based on the respective total amount of dye.
• R 1 , R 2 or R 3 may be linear or branched and are for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl. Methyl and ethyl are preferred.
• R is preferably -COOR 1 or -CONR 2 R 3 , with R 1 , R 2 and R 3 being more particularly hydrogen.
• Alkali metal M is more particularly lithium, sodium, and potassium; M as an equivalent of an alkaline earth metal is more particularly the equivalent of calcium. Preferably M is hydrogen or sodium.
• the dyes of the formula (1 ) according to the invention can be used alone, but more particularly are used in a mixture with other reactive dyes.
• the present invention accordingly also provides dye mixtures which comprise a dye of the formula (1 ) and at least one further fiber-reactive dye.
• Suitable fiber-reactive dyes which can be used in a mixture with the dyes of the formula (1 ) include in principle all known fiber-reactive dyes. These dyes are known to a person skilled in the art and are described comprehensively in, for example, the Colour Index, published by the British Society of Dyers and Colourists and the American Association of Textile Chemists, and in other relevant works.
• the mixing ratio between the dyes of the formula (1 ) and further fiber-reactive dyes may vary within wide limits and is situated for example at 1 : 99 to 99 : 1 % by weight.
• Preferred mixing ratios are 5 : 95 to 95 : 5% by weight, 10 : 90 to 90 : 10% by weight, 20 : 80 to 80 : 20% by weight, 25 : 75 to 75 : 25% by weight, 30 : 70 to 70 : 30% by weight, 40 : 60 to 60 : 40% by weight, 45 : 55 to 55 : 45% by weight, and 50 : 50% by weight.
• Preferred fiber-reactive dyes which can be used in a mixture with the dyes of the formula (1 ) are the dyes of the formula (2)
• R 4 is hydrogen, methyl, methoxy or sulfo;
• R 5 is hydrogen, acetyl or carbonylamido;
• n is 0 or 1 ;
• m is 0, 1 , 2 or 3;
• X is halo, preferably fluoro or chloro
• R 6 and R 7 are hydrogen, methyl or ethyl
• Particularly preferred dyes of the formula (2) are the dyes of the formulae (2a) to (2h)
• M in each case is defined as stated above and is preferably hydrogen or sodium.
• Mixtures of dyes of the formula (1 ) and dyes of the formula (2) are, more particularly, yellow- to orange-dyeing mixtures.
• the mixing ratio of dye of the formula (1 ) to dye of the formula (2) is more particularly between 1 : 99 and 50 : 50% by weight. 10 : 90, 20 : 80 and 30 : 70% by weight are typical mixing ratios.
• R 8 and R 9 independently of one another are hydrogen, methyl, ethyl, methoxy or ethoxy; and p is 0 or 1 ; and Z and M are defined as stated above.
• Particularly preferred dyes of the formula (3) are the dyes of the formulae (3a) to (3d)
• M is in each case defined as stated above and is preferably hydrogen or sodium.
• R 10 and R 11 independently of one another are hydrogen, methyl, ethyl, methoxy or ethoxy; and q is O or 1 ;
• Particularly preferred dyes of the formula (4) are the dyes of the formulae (4a) to (4c)
• M in each case is defined as stated above and is preferably hydrogen or sodium.
• Particularly preferred dye mixtures of the invention comprise a dye of the formula (1 ) together with a dye of the formula (3) and/or a dye of the formula (4) and are deep black-dyeing.
• Deep black-dyeing mixtures comprising dyes of the formulae (1 ), (3), and (4) comprise more particularly dye of the formula (1 ) in amounts of 5% to 40% by weight, dye of the formula (3) in amounts of 50% to 90% by weight, and dye of the formula (4) in amounts of 5% to 40% by weight.
• 20 : 60 : 20, 15 : 70 : 15 and 20 : 65 : 15% by weight are typical mixing ratios.
• the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention can be present as a preparation in solid or liquid (dissolved) form.
• they contain, in general, the electrolyte salts customary in the case of water-soluble and, in particular, fiber-reactive dyes, such as sodium chloride, potassium chloride and sodium sulfate, and may further contain the auxiliaries customary in commercial dyes, such as buffer substances capable of setting a pH in aqueous solution between 3 and 7, such as sodium acetate, sodium borate, sodium bicarbonate, sodium dihydrogenphosphate, sodium tricitrate and disodium hydrogenphosphate, small amounts of siccatives or, if present in liquid, aqueous solution (including a content of thickeners of the type customary in print pastes), they may also contain substances which ensure a long life for these preparations, for example mold preventatives.
• the electrolyte salts customary in the case of water-soluble and, in particular, fiber-reactive dye
• the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention are present as a dye powder containing 20% to 85% by weight, based on the dye powder/preparation, on an electrolyte salt that is also known as a standardizer.
• These dye powders may further contain the aforementioned buffer substances in a total amount of up to 10% by weight, based on the dye powder.
• the total dye content in these aqueous solutions will be up to about 50% by weight, as for example between 5% and 50% by weight, and the electrolyte salt content in these aqueous solutions is preferably below 10% by weight, based on the aqueous solution;
• the aqueous solutions (liquid preparations) can contain the aforementioned buffer substances in an amount which is generally up to 10% by weight and preferably up to 2% by weight.
• the dyes of the formula (1 ) according to the present invention are obtainable in a conventional manner, for instance through synthesis by means of customary diazotization and coupling reactions using appropriate components in a manner familiar to one skilled in the art and using the requisite proportions.
• the dyes of the formula (1 ) according to the present invention are obtainable by diazotizing a compound of the formula (5)
• the dye mixtures according to the present invention can be prepared by customary procedures which are known to one skilled in the art: for example, by mechanical mixing of the individual dyes, which may be in the form of dye powders or granules or in the form of aqueous solutions, for example as-synthesized solutions which may still comprise customary auxiliaries.
• the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention have useful application properties and can be used for dyeing and printing materials comprising carboxamido and/or hydroxyl groups.
• the materials mentioned can be for example in the form of sheetlike structures such as paper and leather, in the form of films, such as polyamide films for example, or in the form of a bulk composition, as of polyamide or polyurethane for example. Particularly, however, they are present in the form of fibers of the materials mentioned.
• dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention are used for dyeing and printing cellulosic fiber materials of any kind. They are preferably also useful for dyeing or printing polyamide fibers or blend fabrics composed of polyamide with cotton or with polyester fibers. It is also possible to use the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention to print textiles, paper or other materials by the inkjet process.
• the present invention accordingly also provides for the use of the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention for dyeing or printing materials comprising carboxamido and/or hydroxyl groups, or rather methods of dyeing or printing such materials in a conventional manner, by using one or more dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention as a colorant.
• the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention provide dyeings having very good fastness properties on these materials, preferably fiber materials.
• the as-synthesized solutions of the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention can be used directly as a liquid preparation for dyeing, if appropriate after addition of a buffer substance and if appropriate after concentration or dilution.
• Fiber materials or fibers in the context of the present invention are in particular textile fibers which can be present as woven fabrics, yarns or in the form of hanks or wound packages.
• Examples of materials comprising carboxamido groups are synthetic and natural polyamides and polyurethanes, in particular in the form of fibers, for example wool and other animal hairs, silk, leather, nylon-6,6, nylon-6, nylon-11 and nylon-4.
• Materials comprising hydroxyl groups are those of natural or synthetic origin, for example cellulose fiber materials or their regenerated products and polyvinyl alcohols.
• Cellulose fiber materials are preferably cotton, but also other vegetable fibers, such as linen, hemp, jute and ramie fibers.
• Regenerated cellulose fibers are for example staple viscose and filament viscose.
• the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention can be applied to and fixed on the materials mentioned, in particular on the fiber materials mentioned, by following the application techniques known for water-soluble and particularly for fiber-reactive dyes.
• dyeings having very good color yields are obtained by exhaust methods from a short liquor as well as from a long liquor, by using various acid- binding agents and if appropriate neutral salts, such as sodium chloride or sodium sulfate.
• the liquor ratio can be selected within a wide range and is for example between 5:1 and 100:1 , preferably between 5:1 and 30:1.
• Dyeing is preferably done in an aqueous bath at temperatures between 40 and 105 0 C, if appropriate at a temperature of up to 130 0 C under superatmosphehc pressure, and if appropriate in the presence of customary dyeing auxiliaries.
• One possible procedure is to introduce the material into the warm bath and to gradually heat the bath to the desired temperature and complete the dyeing operation.
• the neutral salts which speed up the exhaustion of the dyes can also if desired only be added to the bath after the actual dyeing temperature has been reached.
• Padding processes likewise provide excellent color yields and a very good color buildup on cellulose fibers, the dyes being fixable in a conventional manner by batching at room temperature or elevated temperature, for example at up to about 60°C, by steaming or by means of dry heat.
• customary printing processes for cellulose fibers which can be carried out in one step, for example by printing with a print paste comprising sodium bicarbonate or some other acid-binding agent, and by subsequent steaming at 100 to 103 0 C, or in two steps, for example by printing with a neutral or weakly acidic print paste and then fixing either by passing the printed materials through a hot electrolyte- containing alkaline bath, or by overpadding with an alkaline electrolyte-containing padding liquor and subsequent batching or steaming or dry heat treatment of the alkali-overpadded material, produce strong color prints with well-defined contours and a clear white ground. The outcome of the prints is affected little by variations in the fixing conditions.
• thermofix processes When fixing by means of dry heat by following the customary thermofix processes, hot air at 120 to 200°C is used. In addition to the customary steam at 101 to 103°C, it is also possible to use superheated steam and high-pressure steam at temperatures of up to 160 0 C.
• the acid-binding agents which effect the fixation of the dyes on the cellulose fibers are for example water-soluble basic salts of alkali metals and likewise alkaline earth metals of inorganic or organic acids or compounds which liberate alkali in the heat.
• Particularly suitable are the alkali metal hydroxides and alkali metal salts of weak to medium inorganic or organic acids, the preferred alkali metal compounds being the sodium and potassium compounds.
• Such acid-binding agents are for example sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium formate, sodium dihydrogenphosphate, disodium hydrogenphosphate, sodium trichloroacetate, waterglass or thsodium phosphate.
• the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention are notable for outstanding color strength and a steep course of the buildup curve on cellulose fiber materials when applied in the familiar dyeing and printing processes.
• the dyeings and prints obtainable with the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention on cellulose fiber materials further have good lightfastness and, in particular, good wetfastnesses, such as fastness to washing, milling, water, seawater, crossdyeing and acidic and alkaline perspiration, also good fastness to pleating, hotpressing and rubbing.
• the dyeings and prints obtained following the customary aftertreatment of rinsing to remove unfixed dye portions further exhibit excellent wetfastnesses, in particular since unfixed dye portions are easily washed off because of their good solubility in cold water.
• the dyes of the formula (1 ) according to the present invention and the dye mixtures according to the present invention can also be used for the fiber- reactive dyeing of wool.
• Wool which has been given a nonfelting or low-felting finish (cf. for example H. Rath, Lehrbuch der Textilchemie, Springer-Verlag, 3rd edition (1972), pages 295-299, especially finished by the Hercosett process (page 298); J. Soc. Dyers and Colourists 1972, 93-99, and 1975, 33-44) can be dyed to very good fastness properties.
• the process of dyeing on wool is here carried out in a conventional manner from an acidic medium.
• acetic acid and/or ammonium sulfate or acetic acid and ammonium acetate or sodium acetate can be added to the dyebath to obtain the desired pH.
• a customary leveling agent for example a leveling agent based on a reaction product of cyanuhc chloride with three times the molar amount of an aminobenzenesulfonic acid and/or of an aminonaphthalenesulfonic acid or on the basis of a reaction product of for example stearylamine with ethylene oxide.
• the dye according to the invention is preferably subjected to the exhaust process initially from an acidic dyebath having a pH of about 3.5 to 5.5 under pH control and the pH is then, toward the end of the dyeing time, shifted into the neutral and optionally weakly alkaline range up to a pH of 8.5 to bring about, especially for very deep dyeings, the full reactive bond between the dyes of the mixture according to the invention and the fiber. At the same time, the dye portion not reactively bound is removed.
• the procedure described herein also applies to the production of dyeings on fiber materials composed of other natural polyamides or of synthetic polyamides and polyurethanes. These materials can be dyed using the customary dyeing and printing processes described in the literature and known to one skilled in the art (see for example H. -K. Rouette, Handbuch der Textilveredlung, Deutscher fraverlag GmbH, Frankfurt/Main).
• the material to be dyed is introduced into the bath at a temperature of about 40 0 C, agitated therein for some time, the dyebath is then adjusted to the desired weakly acidic, preferably weakly acetic acid, pH and the actual dyeing is carried out at a temperature between 60 and 98°C.
• the dyeings can also be carried out at the boil or in sealed dyeing apparatus at temperatures of up to 106 0 C. Since the water solubility of the dyes of the formula (1 ) according to the invention and the dye mixtures according to the present invention is very good, they can also be used with advantage in customary continuous dyeing processes. The color strength of the dyes of the formula (1 ) according to the invention and the dye mixtures according to the present invention is very high.
• the present invention also provides inks for digital textile printing by the inkjet process, comprising one or more dyes of the formula (1 ) according to the present invention, or a dye mixture of the invention.
• the inks of the present invention contain dye of the formula (1 ) according to the present invention and the dye mixture according to the present invention in amounts of for example 0.1 % to 50% by weight, preferably in amounts of 1 % to 30% by weight and more preferably in amounts of 1 % to 15% by weight, based on the total weight of the ink.
• a conductivity of 0.5 to 25 mS/m can be set by adding an electrolyte.
• Useful electrolytes include for example lithium nitrate and potassium nitrate.
• the inks of the present invention can contain organic solvents in a total amount of 1 -
• Suitable organic solvents are for example alcohols, for example methanol, ethanol, 1 -propanol, isopropanol, 1 -butanol, tert-butanol, pentyl alcohol, polyhydric alcohols for example: 1 ,2-ethanediol, 1 ,2,3-propanetriol, butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 1 ,2-propanediol, 2,3-propanediol, pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, hexanediol, D,L-1 ,2-hexanediol, 1 ,6-hexanediol, 1 ,2,6-hexanetriol, 1 ,2-octanediol, polyalkylene glyco
• the inks of the present invention may further contain customary additives, for example viscosity moderators to set viscosities in the range from 1.5 to 40.0 mPas in a temperature range from 20 to 50 0 C.
• Preferred inks have a viscosity of 1.5 to 20 mPas and particularly preferred inks have a viscosity of 1.5 to 15 mPas.
• Useful viscosity moderators include rheological additives, for example: polyvinylcaprolactam, polyvinylpyrrolidone and their copolymers, polyether polyol, associative thickeners, polyurea, polyurethane, sodium alginates, modified galactomannans, polyetherurea, polyurethane, nonionic cellulose ethers.
• the inks of the invention may include surface-active substances to set surface tensions of 20 to 65 mN/m, which are adapted if necessary as a function of the process used (thermal or piezo technology).
• Useful surface-active substances include for example: all surfactants, preferably nonionic surfactants, butyldiglycol and 1 ,2-hexanediol.
• the inks may further include customary additives, for example substances to inhibit fungal and bacterial growth in amounts from 0.01 to 1 % by weight based on the total weight of the ink.
• the inks of the invention may be prepared in a conventional manner by mixing the components in water.
• the inks of the invention are useful in inkjet printing processes for printing a wide variety of pretreated materials, such as silk, leather, wool, cellulosic fiber materials of any kind and polyurethanes, and especially polyamide fibers.
• the printing inks of the invention are also useful for printing pretreated hydroxyl- or amino-containing fibers present in blend fabrics, for example blends of cotton, silk, wool with polyester fibers or polyamide fibers.
• the auxiliaries have to be applied to the textile substrate in a separate pretreatment step.
• the pretreatment of the textile substrate for example cellulose and regenerated cellulose fibers and also silk and wool, is effected with an aqueous alkaline liquor prior to printing.
• alkali for example sodium carbonate, sodium bicarbonate, sodium acetate, thsodium phosphate, sodium silicate, sodium hydroxide
• alkali donors such as, for example, sodium chloroacetate, sodium formate
• hydrotropic substances such as, for example, urea
• reduction inhibitors for example sodium nitrobenzenesulfonates
• thickeners to prevent flowing of the motives when the printing ink is applied, for example sodium alginates, modified polyacrylates or highly ethehfied galactomannans.
• pretreatment reagents are uniformly applied to the textile substrate in a defined amount using suitable applicators, for example using a 2- or 3-roll pad, contactless spraying technologies, by means of foam application or using appropriately adapted inkjet technologies, and subsequently dried.
• the textile fiber material is dried at 120 to 150 0 C and subsequently fixed.
• the fixing of the inkjet prints prepared with reactive dyes may be effected at room temperature or with saturated steam, with superheated steam, with hot air, with microwaves, with infrared radiation, with laser or electron beams or with other suitable energy transfer techniques.
• a distinction is made between one- and two-phase fixing processes: In one-phase fixing, the necessary fixing chemicals are already on the textile substrate.
• the prints produced using the inks of the present invention have a high color strength and a high fiber-dye bond stability not only in the acidic region but also in the alkali region, also good lightfastness and very good wetfastness properties, such as fastness to washing, water, seawater, crossdyeing and perspiration, and also good fastness to pleating, hotpressing and rubbing.
• the examples hereinbelow serve to illustrate the invention. Parts and percentages are by weight, unless otherwise stated. Parts by weight relate to parts by volume as the kilogram relates to the liter.
• the compounds described in the examples in terms of a formula are indicated in the form of the sodium salts, since they are generally prepared and isolated in the form of their salts, preferably sodium or potassium salts, and used for dyeing in the form of their salts.
• the starting compounds described in the examples hereinbelow can be used in the synthesis in the form of the free acid or likewise in the form of their salts, preferably alkali metal salts, such as sodium or potassium salts.
• Example 4 to 15 of the general formula (1d), with the definitions for D as stated in the table, can be prepared in the same way as in example 1. (1d)
• the dyed fabric is neutralized at 40 0 C in 1000 parts of an aqueous solution which contains 1 part of 50% acetic acid for 10 minutes. It is rinsed again with deionized water at 70°C and then soaped off at the boil with a laundry detergent for 15 minutes, rinsed once more and dried to provide an orange dyeing having very good fastness properties.
• Example 17 4 parts of the dye obtained as per example 1 and 50 parts of sodium chloride are dissolved in 998 parts of water and 5 parts of sodium carbonate, 2 parts of sodium hydroxide (in the form of a 32.5% aqueous solution) and if appropriate 1 part of wetting agent are added. This dyebath is entered with 100 g of a woven cotton fabric. The rest of the processing is carried out as reported in example 16 to provide an orange dyeing of high color intensity and having very good fastness properties. Similar results are obtained when the process described is repeated with the dyes obtained as per examples 2 to 15.
• a textile fabric consisting of mercerized cotton is padded with a liquor containing 35 g/l of anhydrous sodium carbonate, 100 g/l of urea and 150 g/l of a low viscosity sodium alginate solution (6%) and then dried.
• the wet pickup is 70%.
• the thus pretreated textile is printed with an aqueous ink containing
• a textile fabric consisting of mercerized cotton is padded with a liquor containing
• Example 20 The print is then rinsed warm, subjected to a fastness wash with hot water at 95°C, rinsed warm and then dried. The result is an orange print having excellent service fastnesses.
• Example 20 The print is then rinsed warm, subjected to a fastness wash with hot water at 95°C, rinsed warm and then dried. The result is an orange print having excellent service fastnesses.
• a textile fabric consisting of mercerized cotton is padded with a liquor containing
• Examples 21 to 30 below relate to inventive dye mixtures which are prepared by mechanical mixing of the stated dyes in the stated mixing ratios.
• the dye mixtures yield yellow or golden yellow dyeings.
• Examples 31 to 47 below relate to further inventive dye mixtures which are prepared by mechanical mixing of stated dyes in the stated mixing ratios.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Materials Engineering (AREA)
• Life Sciences & Earth Sciences (AREA)
• Textile Engineering (AREA)
• Wood Science & Technology (AREA)
• Coloring (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Ink Jet (AREA)
• Ink Jet Recording Methods And Recording Media Thereof (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 2008
  • 2008-12-09 DE DE102008054404A patent/DE102008054404A1/de not_active Withdrawn
• 2009
  • 2009-11-24 JP JP2011538947A patent/JP2012511591A/ja not_active Withdrawn
  • 2009-11-24 BR BRPI0922855A patent/BRPI0922855A2/pt not_active Application Discontinuation
  • 2009-11-24 EP EP09763915A patent/EP2376578B1/en not_active Not-in-force
  • 2009-11-24 CN CN200980149440.0A patent/CN102245712B/zh not_active Expired - Fee Related
  • 2009-11-24 KR KR1020117012849A patent/KR101597856B1/ko active IP Right Grant
  • 2009-11-24 MX MX2011006080A patent/MX2011006080A/es active IP Right Grant
  • 2009-11-24 ES ES09763915T patent/ES2398193T3/es active Active
  • 2009-11-24 WO PCT/EP2009/065682 patent/WO2010066570A2/en active Application Filing
  • 2009-11-24 PT PT97639157T patent/PT2376578E/pt unknown
  • 2009-12-07 TW TW098141708A patent/TWI478984B/zh not_active IP Right Cessation
• 2011
  • 2011-06-06 HN HN2011001510A patent/HN2011001510A/es unknown
  • 2011-11-25 HK HK11112811.9A patent/HK1158242A1/zh not_active IP Right Cessation

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